


If You're Gonna Be a Square (You Ain't-a Gonna Go Anywhere)

by Kasuchi



Category: Brooklyn Nine-Nine (TV)
Genre: F/M, Friendship/Love, Hook-Up, New York City
Language: English
Status: Completed
Published: 2014-03-04
Updated: 2014-03-04
Packaged: 2018-01-14 12:42:58
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,544
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1267003
Author URL: https://archiveofourown.org/users/Kasuchi/pseuds/Kasuchi
Summary: <blockquote class="userstuff">
              <p><em> The whole thing leaves him oddly melancholy.</em> Jake hooks up with a number of women, but finds the experience is varying degrees of satisfying.</p>
            </blockquote>





	If You're Gonna Be a Square (You Ain't-a Gonna Go Anywhere)

**Author's Note:**

> Post-ep for 1x18 "The Apartment". Unbeta'ed at posting, so please point out any errors. Title is from "Mambo Italiano" by Dean Martin.

**in my life**

Jake is barely moved into Gina's old place -- he supposes it's _his_ place now, which weirds him out still -- when he decides to just say, "Fuck it," and goes out for a drink. There's some tiny but crowded bar not too far from the apartment, the black door with the rounded top a little unusual for the scene, so he goes inside and finds out that not only does the place have two pinball machines but it's also Sixpoint night, so Jake is sold. He's perching on a barstool, rolling his pint glass on the rough-hewn bartop, when a woman in a bright red dress and dark, curly hair falling over her shoulders. She orders the stoutest thing on the draft list and Jake is already half in love.

"Hi," he says. "I'm Jake, and I just moved here." Hey, he's never been above lying before, and Jack Tracktive was not the worst pseudonym he's ever come up with.

"I'm Monica," she says, green eyes gleaming in the light. 

They end up connecting over beers and then pinball, where Jake attempts to impress her with his excellent wrist strength. To which she responds by ducking under his arm and sitting on the machine. Suffice it to say, the game is forgotten until they get asked to leave for hogging the Indiana Jones pinball for their makeout session. Jake's 97% sure he'll be back.

They end up not really going past second base on the couch Jake now owns because he inherited it from Gina in the move. He eats her out while his phone shuffles through his Beatles playlist, and she comes during the string of "na-na-na-na"s at the end of Hey Jude.

**by my side**

Erica is "Taxi Girl" in his phone for a ridiculous amount of time. They meet while Jake is hailing one of thoes green boro cabs after a night out with some academy buddies at a bar in Williamsburg when the petite young woman sporting a pretty cute hi-top fade comes up to him and asks if she can share his cab, since she's going to Park Slope, too. He takes a look at her in her flowy yellow dress and red heels and beckons her in.

They end up kissing up all flights to his apartment and then up the short stairs-slash-ladder to his lofted bed. It ends up being one of the best nights of Jake's recent memory, and he straight up tells her that when his heart stops threatening to pound out of his chest. She laughs, teeth bright white against her darker complexion, and Jake feels his body fully gear up for a second round. 

When it's ridiculous late (or early, given the faintest tinge of green to the sky) Erica kisses him long and slow and lingering, then puts her clothes back on (despite his protests) and slips out into the night. Unexpectedly, Jake finds he misses the feeling of her tucked into his side, the way her shoulders had curved just so, fitting against his chest. The whole thing leaves him oddly melancholy. 

It's almost too good to share, so he only tells bits and pieces of it to his coworkers on Monday. Santiago, though, gives him a look at that makes him think maybe she can see right through him.

**what i need**

The day ends on a sour note, so he goes out with the team and drinks more than he usually does when out with the crew.

"Should you really be drinking that much?" Santiago asks, eyebrow raised, sipping daintily at her Manhattan, her lips puckered around the two tiny red straws. Jake can't stop staring at her mouth, and she's starting to notice, so he tries a distraction. 

"Yes, _Mom_ , it's fine." He knocks back the rest of...whatever it was...and sets the glass back down on the table, shaking his head to clear it. All it does is make the room spin a bit faster. 

"I thought you swore off whiskey," she butts in again, but she's smiling and Jake _really_ has to stop staring at her mouth or at her (for once, down around her shoulders) hair or just at Amy Santiago at all. 

This is when Jake realizes he's definitely drunk.

"Tonight's an exception," he retorts, then gets to his feet. "H'okay, I'm gonna....go that way." He points at a group of pretty young women. "Don't follow me," he adds, not bothering to sugarcoat the statement. Drunk Jake is kind of a jerk, his fuzzy brain notes.

Amy looks startled for a second, then a bit downcast. "Ah, yeah, I should go home anyway." She then pulls out the tiny red straws and does the most amazing thing: she basically knocks back half her Manhattan in one drink, then sets the glass back down on the bartop. She slides the bartender some cash and gets up. "Good luck, Jake." She manages a smile and then she's gone.

Jake feels like a jerk for, well, being a jerk, but he's drunk and day the had been shitty anyway, so he sidles up to some ladies and gets his flirt on.

He takes home Rita, who's 5'6" in kitten heels and with the most hourglass figure he's seen outside of a Kardashian episode. He's _just_ this side of wrecked, so he barely remembers the sex, but he _does_ remember nearly calling her Amy, remembers thinking how her hair was probably like his partner's, getting distracted by Amy's hurt expression while he kisses the hell out of this girl, trying to drown out his drunken id rambling on about his very attractive partner. 

The next day he shows up to work disheveled and looking like hell.

"You look like hell," Santiago says by way of greeting. If he were less hung over, he'd probably have noted the frost on the edge of her voice.

"I deserved that," he acknowledges. "Santiago, I'm sorry about last night. I was a jerk to you because I had a crappy day yesterday and you didn't deserve that." 

She looks a little startled. "You shouldn't get laid more often," she blurts out, then claps a hand over her mouth.

He doesn't even have the energy to tease her. "Oh, I got laid," he replies bluntly, falling gracelessly into his chair. "I just couldn't stop thinking about you the whole ti--" He freezes, glad that this time the entire precinct isn't listening in on their conversation, and feels his entire body tick up five degrees. He's certain he's bright red from the tips of his ears all the way to his toes. "I didn't me--"

She holds up a hand, eyes gleaming with mirth and something else he can't quite identify. "I think you're probably still drunk, Peralta," she says, a little over-loud. 

He stands abruptly. "I think I left something in the records room four days ago," he offers, not even bothering with a good cover. He pivots on his heel and is striding for the bullpen gate when he feels fingers wrap around his elbow, and he freezes. 

"Jake," she says, tugging on his arm slightly so that he has to turn and face her. His face still feels a little too close to tomato for his own security, and she might be right and he might still be drunk, but he figures liquid courage is still liquid courage, so he meets her eyes. Her smile is toned down from megawatt to something else. There's no other word for it: her expression is _soft_. "Apology accepted," she says quietly, then lets him go.

He feels his heart start to race and, before he can contemplate that too much, he heads for the records room. There have to be some cold cases or something. Cold leads. Cold, cold, _cold_.

**all i see**

The money's gone for the month, so Jake is sprawled out on the bed in his loft watching porn. The actress, Tina Landershire, is making pouty faces and breathy moaning noises when his phone dings. With his, ah, _unoccupied_ hand, he pauses the "movie" and picks up his cell. 

_Ready for a second date?_ reads the text. His phone says it's from Taxi Girl. Without hesitation, he texts back, _Yes, absolutely I am._

She comes over again and it's a repeat of the first time. He makes her come so hard, he swears she _meows_ , and he teases her about it between languorous kisses. When Erica leaves this time -- later than before, as the sun is above the horizon this time, but still far too early for Jake's liking, something he hasn't felt about the others -- that creeping emptiness seeps into his bones again.

He talks up the meowing thing during lunch on Monday. "I'm just that good at sex," he tells Santiago, waggling his eyebrows at her. She rolls her eyes and keeps calmly eating her sandwich, flipping through a file.

**in the sun**

He tries jogging for about ten minutes before giving up and getting a hot dog from one of the vendors parked in Prospect Park. It's a gorgeous spring day, the likes of which he's pretty sure most of them had forgotten existed after the neverending winter that had just passed. He munches on the hot dog while walking through the park, veering away from the paved paths onto the packed-dirt byways. 

He remembers walking through here with his dad, and later (though less frequently) his mom. They'd actually walked through the park in silence after he'd graduated from the academy, a cloudy day in mid-September, him in dress blues. 

That's when he runs into Sandra. As in, literally runs into her. They bump into each other and he gets mustard all over what he quickly realizes is her bare chest. Breast. Idly, some still-functioning part of his brain notes that the two words kind of rhyme.

"Oh," he says, power of speech wholly lost. 

She laughs and takes the napkins out of his slack fingers and cleans herself off. "No worries, it happens. Fortunately, it's not like you ruined what I was wearing. She laughs brightly, which Jake join in weakly. He'd forgotten about this phenomenon, though he supposed, living in Park Slope, he should have remembered. 

"I haven't been a beat cop in eight years," he mutters to himself.

"Sorry?"

"Uh, nothing! Hi, I'm Jake. Sorry about that." 

"Sandra," she says, flattening out the first A with her Chicago accent. "I moved here about a month ago and I'm still getting little Butler used to it." At her feet, a dog barked loudly upon hearing its name. Distantly, Jake noted she was wearing flip-flops. And that her toes were painted. 

Later, when he's telling this to the team, Gina butts in. "So, did you get her number? I bet she's some kind of, like, hippie granola girl and into some freaky stuff." 

"Hipsters," Rosa says flatly, crossing her arms over her chest. 

"Dogs," Amy shudders. 

"What kind of mustard?" Charles asks, guileless.

Jake shrugs, ignoring Charles's question. "Nah, she had a Yorkie, and I'd already seen her boobs, so there really wasn't much left in it for me." Amy smacks him on the shoulder. "Ow! What?"

**all night long**

Mary is twenty-two on the outside, all long legs and long hair, and she laughs at everything Jake says, which is awesome for a while but starts to grate on Jake's nerves maybe twenty minutes in. The last statement he'd made was about a recent, gruesome murder he'd solved over by the Gowanus Canal, and the girl had just kept laughing, making Jake think she wasn't really paying attention. He's trying to plot a way to gracefully bow out when he feels his phone buzz, and he pulls it out. He's never wanted a murder to have happened more in his life.

_Kylie and I are at the please bergen, yuo shloud come hnag out!!_

In spite of himself, he grins broadly. He tells Laughing Mary he's sorry but he's gotta go, then practically sprints to the train. For once, luck is on his side, and the G arrives without too much delay. When he resurfaces, he ambles towards the Plea Bargain, attempting to savor the moment.

A (very, by the sounds of it) drunk Amy Santiago, at the diviest of dive bars. 

He walks in, past a group of smokers out front, and makes his way to the deck in the back, somehow knowing if she's here then she's back there. He's right; she's seated in the back wearing some seafoam green, chiffon top that just seems to move around her (except for the part where it's got no back) and dark skinny jeans with gold heels. It's unnerving because he's seen her date look, and it's not that different from her work look. It's gotta be Kylie's doing. 

He sidles up to her and gently touches her elbow (the safest seeming part of her to touch right now) to get her attention. Her expression brightens when she sees him -- possibly a first? -- and she turns to Kylie and says, "See! He totally came!" 

Jake raises an eyebrow at that and Kylie bursts into drunk-girl giggles, which is actually kind of cute. 

Amy rolls her eyes, though he can tell that if not for the chair she's half-sitting in, she'd probably have rolled onto the floor. "Jake," she says seriously, grabbing his hand. "I need your help." He's a little stunned by her very serious tone that he doesn't respond. Not that it matters; she's rambling on already. "...and you're always pointing out weird skills and stuff that you have so maybe you can help me out."

"Getting close to the point at all, Santiago?"

She grins at that, and Jake ignores the way his stomach flips over at the sight of her smiling so openly at him. "Wanna be my second in pool?"

"Uh, I'm not the best swimmer and--"

She swats him on the arm, but because she'd drunk it hurts maybe a third of what it usually does. "Not in a pool! We're not playing chicken, god."

"You know what that is?"

She levels a flat look at him. "Duh, I went to college." 

He laughs at that. "So you need me to be your partner in billiards? What about Kylie?"

"She's terrible." "I'm _terrible_ ," they chime together, and it sounds a little rehearsed but Jake's not gonna push. 

"How do you know I'm any good?"

"I don't," Amy says bluntly. "But you pay attention and you're smart, so I'm taking a risk."

"That's....the nicest thing you've ever said to me." 

"Play decent pool and she's say more stuff," Kylie chirps, before drinking the rest of her wineglass in one long drink. "Oops, I'm out. Be right back!" She disappears into the thick of it, pushing her way to the bar. Presumably.

"We're not going to see her again for the rest of the night, are we?"

Amy shakes her head, tottering to the pool table. "Nope. Some guy will chat her up and take her home, probably. That's what usually happens."

"Leaving you to play pool?"

"Leaving _us_ to play pool." She grins again and hands him a cue stick like it's Excalibur or something, and Jake gives her a long look before he takes it, because it feels like something shifted while she was talking, and Jake's not sure he's still on solid ground. 

So he tries a joke. "Wanna fleece some hipsters?" 

"I thought you'd never ask." 

They hustle pool for about an hour and a half, playing through three racks before the bar catches on, but not before they make enough to pay the tab and tip the bartender just before last call. Jake is pleasantly buzzed and Amy is approaching shitfaced, but she's still keeping it together by some miracle. 

"You are _so_ drunk," he says, half-laughing, arm around her waist. He's walking her back to her place -- thankfully nearby -- and her heels are tripping her up.

"M'not," she insists. "These, shtupid heels. Kylie made me wear them."

"When did you even buy these anyway? I thought you only owned sensible heels."

"Javier's wedding," she replies, holding up one foot to admire the shoe. Jake tightens his hold on her waist to keep her from toppling them both over. "I was Maria's bridesmaid, and we had to buy the shoes." 

"Yes, but why'd you keep them."

"Thought they were pretty," she manages. "Made me feel pretty."

"You're very pretty, Amy," Jake says seriously. "Even without gold shoes." 

"You think I'm pretty?" She grins. "I _knew_ it!" She looks as satisfied as she did when he wrote her that letter of recommendation.

"This is my nightmare," he mutters, the déjà vu lost on him. . "Okay, stairs, c'mon, you can do it."

"I'm drunk, Jake, not suddenly five." She straightens, takes a breath, and walks up the short flight of stairs to her front door without issue, Jake right behind her just in case. "Thanks for walking me home."

"Thanks for texting me. I have _so_ much blackmail material now, you have no idea."

She rolls her eyes and reaches for her door. "See you tomorrow," she says, and lets herself in. He waves and then heads back to the street, walking along Fulton to Flatbush Ave, trying _not_ to berate himself for not kissing her when he had the chance. 

**here i am**

"I think I'm getting old," Jake says when he sits down at his desk, Santiago already caffeinated and perched on the edge of her chair. 

"Back pop when you got outta bed this morning?" She barely glances at him as she clicks through emails. 

"Wait is that how most people know? Ugh, I've had that since I was in the academy. No, I mean, I went on a date last night and just, I dunno."

She stops clicking and turns off her monitor, focusing on him. "What do you mean?"

"Well, her name was Jessica. She's half-Jewish, Mets fan, lifelong New Yorker, basically perfect. And we had a really nice time, dinner was great, and the sex was good, too."

Amy wrinkles her nose. "Ew, spare me." 

He rolls his eyes. "Anyway, nothing went wrong, but after, I dunno. It just felt....empty." He shrugged and drummed his fingers on his desk. "And I think that's been happening for a while now."

"Since Taxi Girl?" She shoots him a knowing look. "Congratulations, you're entering adulthood."

"Uh, I already did that at my bar mitzvah."

She shakes her head. "Jake. Maybe you're hitting the point where you want a mature, adult relationship with someone. And not just _someone_ , but the right person. It's a good thing. You should embrace it."

"A mature, adult relationship, huh? Sounds boring." 

She sighs. "Well, I tried." She turns her monitor back on and resumes clicking through her emails. Surreptitiously, Jake watches her and considers.

**makes me your man**

He's got a fistful of her hair and he can feel her fingers digging into the muscles of his shoulder, nails scratching lines down his shoulder blades and making him shiver. 

"Amy," he breathes, breaking the kiss to look at her, thumb tracing her bottom lip while his other fingers splayed on her neck. He could see her pulse beating erratically, and her breath came in gasps. 

"Don't wuss out now, Jake," she says firmly. It makes him laugh and shatters the tension of the moment. He pulls away and pulls off his shirt, grinning when he sees her mirroring his actions. 

"Is this what you meant when you told me I should try for a mature, adult relationship?"

"Shut up and get naked," she commands.

He gives a low whistle. "Someone is _bossy_." 

She shoots him a look that was somewhere between "come hither" and self-satisfied. "But you like it." 

"God help me, I kinda do." He undoes his belt and pulls it out of the loops slowly, the _whoosh_ sound making her lick her lips with anticipation. "You like what you see?"

"I'm just glad you took the captain's advice and stopped overdoing the manscaping."

"Okay, first, we agreed to never bring that up again, and second, no talking about people we work with when we're.....you know."

"Naked?"

"In dishabille," he counters.

"How do you even know that word?"

"One of those fifteen books I read was one of my mom's romance novels." 

"Oh, God. You need to stop talking."

"I can't, it's a nerves thing, I keep saying stuff when I'm nervous."

Her expression softens. "You're nervous?"

"Well, yeah, I mean...it's _us_ , you know?" He goes very still, jeans sliding low on his hips. Unbeknownst to him, Amy finds this _very_ distracting.

"I know, but...I'm just Amy. And you're just Jake. We've both done this dance plenty of times." 

"I _am_ pretty good at this." 

"All I hear is talk, talk, talk." She smirks and enters his personal space, fingers curling into the belt loops of his jeans, pulling his hips into hers. "I have a much better idea what you can do with that mouth of yours." 

"What's that?" he asks, teasing. 

"Practice your penmanship," she replies smartly, before pushing him back onto her bed and crawling over him.

**Author's Note:**

> The working title for this was "Mambo Number Jake" so guess what song this was inspired by.
> 
> Toplessness in New York City is [rather famously not illegal](http://blogs.villagevoice.com/runninscared/2011/06/topless_bowery.php) for either gender. It's still a bit unnerving to run into this person, but it's not considered indecent exposure here. 
> 
> The bar Jake goes to in the first section is based on [Two Door Tavern](https://foursquare.com/twodoortavern). The dive bar where Jake finds Amy is based on [The Alibi](https://foursquare.com/v/the-alibi/439306adf964a520702b1fe3).
> 
> A number of the hookups are based on stories a friend of mine has told me about his, ah, misadventures in the hipster scene in Brooklyn. Jake's transition is also kind of based on what I've watched him choose over the course of our friendship. Fortunately, most men don't read fanfiction, so I'm _probably_ safe! *nervous laughter*
> 
> I posted this without really skimming for mistakes. Please feel free to point out any issues. Thanks for reading. :)


End file.
